


Bobby Singer's Reward

by ArtemisBennet



Series: Crowley's Punishment [2]
Category: Supernatural
Genre: Anal, Crobby - Freeform, Crowley in panties, Crowley is just kinky, Crowley lives! - Freeform, Hand and Finger Kink, I'm Going to Hell, M/M, Teasing, Topping from the Bottom, caressing
Language: English
Status: Completed
Published: 2020-02-20
Updated: 2020-02-20
Packaged: 2021-02-27 22:34:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,115
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22813144
Author URL: https://archiveofourown.org/users/ArtemisBennet/pseuds/ArtemisBennet
Summary: This is a sequel to my story Crowley's Punishment, in a sort of vague AU neverland around sixth season, maybe, when Crowley was working with the Winchesters and conducting a demon/hunter relationship with Bobby Singer. I’d also like to acknowledge my reference and debt to the excellent – and very hot story, The Right Kind of Ridiculous by The Fierce Beast and Violet Smith, which has forever paired Crowley with women’s underwear in my mind. I’d like to think of that story sharing a universe with this one.
Relationships: Crowley/Bobby Singer
Series: Crowley's Punishment [2]
Series URL: https://archiveofourown.org/series/1906933
Comments: 2
Kudos: 45





	Bobby Singer's Reward

**Author's Note:**

> This is a sequel to my story Crowley's Punishment, in a sort of vague AU neverland around sixth season, maybe, when Crowley was working with the Winchesters and conducting a demon/hunter relationship with Bobby Singer. I’d also like to acknowledge my reference and debt to the excellent – and very hot story, The Right Kind of Ridiculous by The Fierce Beast and Violet Smith, which has forever paired Crowley with women’s underwear in my mind. I’d like to think of that story sharing a universe with this one.

He was in Hell, which was as it should be; him being damned and a demon and King of the place. He shouldn’t be thinking of going back above so soon, scant Hell-months after his last trip. For Bobby, it would be….Crowley shifted on his throne, barely hearing the droning on of some demon reporting on something or other…. around two weeks after his last visit.

_Miss me, lover?_

He still got a thrill, even thinking the words, knowing he _could_ say them to Bobby Singer, that Bobby would grumble and blush and delay things, before letting Crowley tease him into bed. And such a time that had been, just gone. Crowley had teased and delayed and even denied himself, in order to wear down Bobby’s control and obtain the response he _needed._ His ass had been sore for _days_ after the pounding Bobby had given him. He smiled reflectively, then shot a chill glare at the reporting demon, who obviously thought the King was pleased with _her._

_On a cold day in my back yard, darling._

This soon, there was little chance Bobby would unleash the beast, so to speak, and probably more that he’d be guilt tripping about how rough he’d been on the previous delightful occasion. 

But now….Crowley breathed in sulphur and the iron stink of blood and terror which permeated the diabolic realm he ruled. Before him were the travellers, the demons of the crossroads who supplied Hell with its souls and its power. His hunter was far away. Denying himself, well, that wasn’t demonic, but it certainly made the end result all the sweeter, if you could use that word about the very physical reward he hoped to enjoy. And the reward he meant to give Bobby, of course, which was him.

The King shifted slightly to ease the pressure in his trousers. All of them were in their meatsuits here; vessels of all ages and types. Costumes to bedevil and lure the humans who possessed the all-necessary souls.

And suddenly it was too much.

Crowley rose to his feet, causing the droning demon to stop talking and give him a wary stare. “That’s all,” the King announced. “I can’t stand listening to you another minute, so why don’t you all get back to work and do something about increasing your pitiful quotas, hmm? I have a very important affair - of state - to take care of.”

And he vanished.

*

He found it to be early evening in that part of the world where Bobby lived. The hunter was at home, beer in hand as he desultorily leafed through some book. He jumped as Crowley, eschewing knocking, rematerialised in front of his armchair. “Shit, Crowley! Don’t _do_ that.”

“Missed you too, lover.”

“And don’t call me that either. What if somebody heard?”

“Robert, there’s no one else in your house. You’re not expecting the pestilent Winchesters, are you?”

“No,” Bobby said suspiciously. “What’re you up to?”

“Do you really need to ask me that after last time?”

Last time had been….intense. Crowley had let the interval drag out, until Bobby had been damn near desperate and _not_ wanting to acknowledge it; willing to give Crowley the rough handling that he craved. The hunter still regarded that as wrong, telling Crowley awkwardly that he wasn’t into that damn stupid dom and sub scene. _Oh, lover,_ the demon thought, _do you_ really _think I’d do anything I don’t want to do? I wish I could make you understand that rough stuff…and pain…makes me feel as though I was truly alive again._

Robert had needed convincing, of course, and careful incitement, but he’d responded with gratifying intensity that made Crowley’s naughty bits ache with delicious recollection. “So this is a booty call, huh?” But Bobby sounded more amused than annoyed. “Still don’t see why you wanta come to me for that, but sure, we can….” And still gruff and awkward, he patted his lap as though thinking Crowley would refuse. In the next moment, it was full of wriggling demon. Bobby’s arms curved around him and he leaned his chin on Crowley’s shoulder with a sigh. “Bad day? Or week? How long’s it been for you?”

“I don’t know, darling.” Crowley closed his eyes, savouring the rare and comforting feeling of strong, muscled arms around him, that hard strength, the smoky scent of Bobby’s clothes and just _him_ , warm and real and there. “I try not to keep track, it’s too depressing.” Like Bobby, he didn’t refer directly to Hell. It was tempting fate, he decided, as though Hell would drag him back – ha ha – and spoil his happiness, the pleasure in Bobby’s company no demon was supposed to feel.

“I reckon I know what you want,” Bobby murmured, rubbing the demon’s other shoulder. “Why don’t you tell me, hm?”

“Why don’t you get on with it, and not worry about asking?” Crowley murmured, shifting himself until he was straddling Bobby, facing him, almost close enough to kiss. 

“You’re really into this sub thing, huh?”

“No, darling, I’m not a submissive.” The demon’s voice was deliberately level as he brought his face close to Bobby’s but did not kiss him. 

“So what do you call it then? I mean, a guy who likes bein’ hurt, that’s kind of… last time you didn’t want to wait for me to lube up!”

“You could call me - an appreciator of the more intense sensations in life, from keenest delight all the way to the agony of flaying one’s soul,” the demon said softly. “My kind don’t have souls any more, love, and we seek to remember how it felt to have them. Those who become demons are those who come to cherish the sensations of the fire and the rack.”

Bobby shivered against him. “That’s….sick, Crowley.”

“What do I want? I want you in me to the hilt.” Crowley angled himself so as to slowly rub his bulge against Bobby’s in a way which had Bobby groaning deeply. “I can feel how much you want to, how good it will feel for both of us. But try, just try, ordering me to do things I _don’t_ want and see where it gets you, hm? _That’s_ a sub. Get your hands on me, darling, _now.”_

Bobby, responding to the note of command, immediately slid his hand between them, under the material of Crowley’s trousers and inside to caress him, making a murmur of surprise as his hand touched flimsy silk. “You’re wearin’ women’s panties again, aren’t you?”

“You seemed to appreciate it so much the last time,” Crowley smirked. “Didn’t have time to find the whole get up, but we can always revisit that later.”

Bobby chuckled, gasping a little. The hunter was, Crowley decided, a most apt pupil. He’d told Crowley he’d always “kinda appreciated” men but had never gotten around to actual experimentation. Once Crowley had led him down that path, so to speak, Bobby’s learning curve had been swift. Now, he slid his fingers under the silk of Crowley’s panties, tight against the considerable package they enclosed, quickly finding what he sought. He stroked, grasped and fondled intimately, then as Crowley whimpered pleasure, gripped him hard and jerked him. “Oh, darling!” Crowley squealed aloud. Encouraged, Bobby tugged harder. 

“Just what kinda stuff do you want me to do?” he murmured.

Crowley chuckled softly; raspy and dark and male. “Everything, darling.”

*

Crowley lay on the floor of Bobby’s living room, naked except for the red silk panties, ready for the man above him. His demons would have been utterly shocked to see him, he knew. They wouldn’t understand how completely he was running the fuck.

His legs were apart and his impressive erection thrust up against the tight silk of those little panties as Bobby pressed close. The hunter’s gaze was fixed on Crowley’s crotch; he reached to trace the bulging outline with one finger, stroking Crowley right over the damp area on the silk where the tip of his dick leaked with excitement. Crowley nearly came on the spot. “Please, darling, fuck me. Fuck me hard!”

Bobby traced upwards to where the panties ended, paused a long moment and took his hand away. “What kinda pain are we talking about here, Crowley? The kind you like, I mean?”

“Something….suitably Hellish will be coming your way, that you won’t like at all, if you don’t keep going, Robert!”

“Now, is that nice? You could try askin’ a bit more politely, for a start.” Bobby sounded actually annoyed with him, now, how could _that_ be? Crowley thought about getting up and then rested his head back down, trying to assemble his scattered thoughts. He breathed carefully, slowly, then lifted his head once more to try to see Bobby’s face. When he did, he swore softly and wonderingly. The bastard was _grinning_. “Yeah, you got me stirred up a bit, but I reckon I can take care of myself just fine. But you got your hopes up there, didn’t you, King of Hell? Come in all hot and bothered, figure Bobby Singer’s gonna do just what you want, like always. You want me to do everythin’ to you, get my face between your legs or my dick into you, give you those _feelings_ all the way through you….well, how’s it gonna feel if I do _nothing_ instead, just watch you lyin’ there in those silly little silk panties?”

Crowley breathed in and out carefully, wondering whether it was possible to explode his meatsuit. He reached a hand down to his own groin, but felt it seized in Bobby’s calloused grip and held firmly, almost painfully. He savoured it, let out another ragged breath. “Let me go, Robert. You know I can make you let me go.”

“And where’s the fun in that?” Bobby asked idly. “Course you can, you got demon powers, you got witch powers with all that studying you do. Proper demon geek, aren’t ya? But you got something with me that you don’t even appreciate.”

“What might that be, Robert?”

“It’s that I want to be with you, not _just_ that I wanta do you.” Finally Bobby moved his big hand back to the swollen bulge in Crowley’s panties and stroked lightly but firmly over it, towards his entrance. Crowley whined softly, desperately and wondered whether it was possible that his mind could just disintegrate. “You don’t want to wreck that, so you’re gonna lie here, no matter what I do or don’t do, aren’t you?”

“Robert?”

“What, Crowley?”

“I truly hate you.”

“You gonna ask nicely? Call me sir?”

“I’m _not_ your damn sub.”

“What was that?”

“Please fuck me, Robert.”

“Please fuck you what?”

“Please fuck me, _sir!_ ”

Bobby took his hand away again, but this time so that he could mount Crowley, letting his dick slide deliciously against Crowley’s own, only the thin silk between them. “Glad we got that sorted,” the hunter growled in his ear. “I was beginning to think you’d hold out.”

“Not really my style, darling.”

With his words and the movements of his stocky body, Crowley teased Bobby Singer’s wakened desires to a peak, until conscious thoughts were in the back seat and lust roared out. Bobby tore at the silk panties to get them off Crowley, pressing forward the moment he had access, fumbling to get his cock in position for entry. 

“I gotta lube, you didn’t…”

“Don’t stop, lover, please don’t wait…”

The hunter did hesitate, then growled, pushing himself in, and the demon shrieked aloud in enjoyment as he was so completely filled. Bobby held his plump legs up, not letting him move, exactly as Crowley had demanded. Crowley saw the hunter’s eyes glaze with bliss as he buried his hard length inside Crowley’s ass. Crowley made no effort at control. He squealed and writhed against the hunter, held down by the weight of the big man over him, as the invading cock pushed repeatedly at his sweet spot.

“I’m not there yet,” Bobby gasped. “You’re stayin’ right there until I come.”

Crowley had lost his words, but he cried out his pleasure. Bobby withdrew from him briefly, only to regroup and ram his cock into Crowley’s hole again, hard and relentless and magnificent, until orgasm overcame him and he pumped himself dry into the willing demon, the man, under him on the ground.

“That….that what you like?” the hunter panted. “That rough enough for you?”

“For now, yes, darling,” Crowley purred in satiation. He slid his arms around Bobby’s burly shoulders and held him close. 

“We still got a problem, Crowley.”

“What’s that, lover?”

“Findin’ something you _don’t_ want me to do to you!”


End file.
